STEREOELECTRONIC EFFECTS AT CARBOXYLATE OXYGEN - SIMILAR BASICITY OF THE E-LONE AND Z-LONE PAIRS IN SOLUTION

被引：22

作者：

ALLEN, FH ^{[1
]}

KIRBY, AJ ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 23期

关键词：

D O I：

10.1021/ja00023a035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Comparisons of effective molarities for intramolecular reactions and bond length-pK(a) correlations show no evidence of a significant difference in basicity between the E and Z lone pairs of carboxylate in the condensed phase.

引用

页码：8829 / 8831

页数：3

共 24 条

[1] BOND LENGTH AND REACTIVITY - VARIABLE LENGTH OF THE C-O SINGLE BOND [J].

ALLEN, FH ;

KIRBY, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6197-6200

[2]

AMOS RD, UNPUB

[3]

BEAGLEY B, 1975, MOL STRUCTURE DIFFRA, V3, P52

[4]

BJARNOV E, 1976, Z NATURFORSCH A, V31, P1113

[5] KINETIC EFFECT OF A SYN-ORIENTED CARBOXYLATE ON A PROXIMATE IMIDAZOLE IN CATALYSIS - A MODEL FOR THE HISTIDINE ASPARTATE COUPLE IN ENZYMES [J].

CRAMER, KD ;

ZIMMERMAN, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3680-3682

[6]

CSIZMADIA IG, 1979, CHEM ACID DERIV 1 SB, pCH1

[7] ON THE IMPORTANCE OF ORIENTATION IN GENERAL BASE CATALYSIS BY CARBOXYLATE [J].

GANDOUR, RD .

BIOORGANIC CHEMISTRY, 1981, 10 (02) :169-176

[8] CONFORMATIONAL POPULATIONS AND ROTATIONAL BARRIERS IN ESTERS [J].

GRINDLEY, TB .

TETRAHEDRON LETTERS, 1982, 23 (17) :1757-1760

[9]

Kirby A.J., 1980, ADV PHYS ORG CHEM, V17, P183

[10] INTRAMOLECULAR PROTON-TRANSFER CATALYSIS OF NUCLEOPHILIC CATALYSIS OF ACETAL HYDROLYSIS - THE HYDROLYSIS OF 8-DIMETHYLAMINO-1-METHOXYMETHOXYNAPHTHALENE [J].

KIRBY, AJ ;

PERCY, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (07) :907-912

← 1 2 3 →